Despite living under the world’s spotlight, Michael Jackson’s love life largely remained a mystery, igniting endless speculation. Captivating headlines throughout the ’80s and ’90s often linked Michael to glamorous Hollywood starlets including Diana Ross and Brooke Shields, but the reality of their love stories were far more complex.
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Here’s the tea behind the romance talk that kept fans guessing throughout the decades, and the real story behind the women he admired and trusted in ways that went beyond romantic labels.
Tatum O’Neal
In the late 1970s, Michael Jackson shared a sweet and early connection with actress Tatum O’Neal, known for her Oscar-winning role in “Paper Moon” (1973), as well as memorable parts in “The Bad News Bears” (1976). During a 2002 interview with Martin Bashir, Michael explained the painfully awkward sexual interaction they had — or lack thereof — which ultimately ended with his hands covering his eyes.
“I did my hands like this, and I wouldn’t let them down,” he explained with his hands over his face. “And she just walked away.”
How Did It End?
Although it was documented that things casually faded out in the 80’s, O’Neal recalled her agent, Sue Mengers, ordering her not to go to Michael’s musical premier of “The Wiz.” “That really upset him,” O’Neal admitted.
“He was never really the same to me after that. And I felt terrible. That broke his heart, it broke my heart. And I could never get it back after that.”
Brooke Shields
In the early ’80s, supermodel and actress Brooke Shields had a bond with Michael that got plenty of headlines — mostly because he was totally smitten with her. During a 2001 conversation with Rabbi Shmuley Boteach, his reported friend and spiritual guide, Michael went on record declaring Shields “One of the loves of my life.”
Those conversations were later compiled into the “Michael Jackson Tapes.”
“I think she loved me as much as I loved her, you know? We dated a lot. We went out a lot. Her pictures were all over my wall, my mirror, everything,” Michael stated, per Entertainment Weekly.
Brooke’s Perspective
It seems some delulu was at play, as Shields reportedly scalded Michael on a phone call for fabricating their romance, adding that his dating claims were “pathetic.” And a kiss? Don’t even think about it. Shields explained that she boldly turned him away during a steamy moment, and had this to say when asked if they ever “dated” or “kissed.”
“No! There was one moment when we were in the car and the cameras were there and he grabbed me to kiss me, and I said, ‘No! Stop! We are just friends and you need me as a friend,’ Shields stated, per the Independent.
“I called him up and I think I said, ‘This is kind of pathetic that you need to do this. I am having a shot at normal life – you cannot drag me into crazy town’.” She continued: “I remember the early days when other actresses were after him and he was kind of cute, before the shift. But it never ever crossed my mind.”
Diana Ross
Motown starlet Diana Ross wasn’t just a friend to Michael Jackson — she was family, a mentor, and one of the biggest influences on his life and career. Their bond started back in the late ’60s when The Jackson 5 opened for her on tour, and it only grew stronger over the decades.
In 1983, Michael went on record saying, “Diana Ross is everything you could wish for, I love her. I hope she marries me. She always tells me her most private secrets. That’s the kind of relationship we have,” per The Detail.
“Remember The Time” Was Dedicated to Diana Ross
Michael’s brother, Jermaine Jackson, recalled that Michael dedicated his hit song “Remember the Time” to Diana Ross. Unlike many of his other videos featuring female love interests, this was the only music video in which Michael is actually shown kissing the woman on screen (and we loved it).
“…that song was, as Michael told me, written with Diana Ross in mind; the one great love that, as far as he was concerned, escaped him,” Jermaine stated, per Medium.
Elizabeth Taylor
Elizabeth Taylor and Michael Jackson weren’t a couple, but their friendship was legendary. Starting in the ’80s, they had a bond that went way beyond Hollywood glam — Elizabeth was Michael’s confidant, always standing by him through the good, the bad, and the crazy.
“We’re very much alike, we both had terrible childhoods. Working at the age of nine is not a childhood. He started at the age of three,” Liz told Larry King. She also added that when Michael was around children, there was “Nothing odd about it,” at all.
More on Liz Taylor and Michael’s Love
Elizabeth Taylor went on record expressing her love for Michael, as did the pop star as well. Although platonic, it’s clear the connection between the two was one for the decades. “I don’t think anyone knew how much we loved each other. The purest, most giving love I’ve ever known,” Liz stated, per True Michael Jackson.
“Elizabeth Taylor is a warm cuddly blanket that I love to snuggle up to and cover myself with. I can confide in her and trust her,” Michael said, per the outlet.
Lisa Marie Presley
Michael Jackson and Lisa Marie Presley — daughter of the legendary Elvis Presley — shocked the world when they married in 1994. While Lisa described their love as genuine, and confirmed to Oprah, “Yes, this is a real marriage,” back in 2005, she also spoke candidly about Michael’s manipulation tactics, deeming it his survival mechanism.
“I always confused that manipulation thinking that it meant he didn’t love me,” she says. “But I understand it better now. The manipulation was a survival tactic for him,” Presley stated, per Oprah.
How Did Michael And Lisa Meet?
Michael Jackson and Lisa Marie Presley met in 1975, when Lisa Marie was a young girl and Michael was touring with The Jackson 5. That said, the two didn’t cross paths romantically until the early 1990s. Their adult relationship began around 1993 after they were introduced again by mutual friends, sparking a romance that led to their marriage in 1994.
Michael Jackson and Lisa Marie Presley, Divorce 1996
The two parted ways when their divorce finalized in 1996, as both superstars came under the pressure of a relentless media firestorm. Presley admitted their marriage was “very intense,” acknowledging the difficulties they faced — including suspicion of drug use — however revealed that she “truly enjoyed being there for him.”
“It was one of the highest points in my life when things were going really well, and he and I were united. It was a very profound time of my life,” she said.
Debbie Rowe
Debbie Rowe — Michael’s second wife — popped on the scene in the mid-1990s as his dermatology nurse, but their relationship quickly became much more complicated — and mysterious. They married in 1996, and she became the mother of two of his children, yet the details of their bond were kept under wraps.
That said, it got messy in the kingdom. Apparently, Michael and Debbie sort of trauma bonded, often discussing their bad luck in love and unhappy marriages, keeping his bond with her away from Lisa Marie, per Medium. According to reports, Lisa did eventually find out, but thought nothing of it due to her plain Jane appearance.
Some speculate their marriage was more of a practical arrangement than a traditional romance, but Debbie has remained an important figure in Michael’s personal life and legacy. Despite the intrigue, Rowe’s role as mother and caretaker is pretty much undeniable.
Michael’s Honorable Mentions
Pop sensation Madonna, supermodel Naomi Campbell, stage legend Liza Minnelli, and powerhouse vocalist Whitney Houston are among the women Michael built friendships with, rooted in mutual respect and shared experiences. While rumors sought to spin sizzling romances onto his friendships, it seems some of these bonds were about trust, collaboration, and support.
Michael’s love wasn’t only romantic, but largely rooted in what appears to be a fierce loyalty, a deep compassion, and mutual understanding.
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